(1-(pyridin-4-yl)ethane-1,2-diyl)bis(phosphonic acid) | 652989-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1-(pyridin-4-yl)ethane-1,2-diyl)bis(phosphonic acid)
• 英文别名: 1-(4-pyridyl)ethane-1,2-bisphosphonate；Phosphonic acid, [2-phosphono-1-(4-pyridinyl)ethyl]-；(2-phosphono-1-pyridin-4-ylethyl)phosphonic acid
• CAS: 652989-82-7
• 化学式: C₇H₁₁NO₆P₂
• 分子量: 267.115
• InChiKey: LMEUGMVMKAWITH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2'-联吡啶-6,6'-二羧酸 、 di-μ-chlorobis-[(η⁶-benzene)chlororuthenium(II)] 、 (1-(pyridin-4-yl)ethane-1,2-diyl)bis(phosphonic acid) 在 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 51.0h， 以68%的产率得到[Ru(2,2'-bipyridine-6,6'-dicarboxylate)((1-(pyridin-4-yl)ethane-1,2-diyl)bis(phosphonic acid))₂]
  参考文献：
  名称：

  Mechanism of water oxidation by [Ru(bda)(L)₂]: the return of the “blue dimer”

  摘要：

  [Ru（bda）L2]（bda为2,2'-联吡啶-4,4'-二羧酸；L为4-哌啶或异喹啉）的活性水氧化催化剂是一个氧桥联的蓝色二聚体中间体，由两个[RuIV-OH] +单体双分子生成。

  DOI：

  10.1039/c4cc07968j
• 作为产物：
  描述：

  4-乙炔基吡啶 在 盐酸 、 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 生成 (1-(pyridin-4-yl)ethane-1,2-diyl)bis(phosphonic acid)
  参考文献：
  名称：

  Effects of Bisphosphonates on the Growth of Entamoeba histolytica and Plasmodium Species in Vitro and in Vivo

  摘要：

  The effects of a series of 102 bisphosphonates on the inhibition of growth of Entamoeba histolytica and Plasmodium falciparum in vitro have been determined, and selected compounds were further investigated for their in vivo activity. Forty-seven compounds tested were active (IC50 < 200 muM) versus E. histolytica growth in vitro. The most active compounds (IC50 similar to 4-9 muM) were nitrogen-containing bisphosphonates with relatively large aromatic side chains. Simple n-alkyl-1-hydroxy-1,1-bisphosphonates, known inhibitors of the enzyme farnesylpyrophosphate (FPP) synthase, were also active, with optimal activity being found with C9-C10 side chains. However, numerous other nitrogen-containing bisphosphonates known to be potent FPP synthase inhibitors, such as risedronate or pamidronate, had little or no activity. Several pyridine-derived bisphosphonates were quite active (IC50 similar to 10-20 muM), and this activity was shown to correlate with the basicity of the aromatic group, with activity decreasing with increasing pK(a) values. The activities of all compounds were tested versus a human nasopharyngeal carcinoma (KB) cell line to enable an estimate of the therapeutic index (TI). Five bisphosphonates were selected and then screened for their ability to delay the development of amebic liver abscess formation in an E. histolytica infected hamster model. Two compounds were found to decrease liver abscess formation at 10 mg/kg ip with little or no effect on normal liver mass. With P. falciparum, 35 compounds had IC50 values <200 muM in an in vitro assay. The most active compounds were also simple n-alkyl-1-hydroxy-1,1-bisphosphonates, having IC50 values around 1 muM. Five compounds were again selected for in vivo investigation in a Plasmodium berghei ANKA BALB/c mouse suppressive test. The most active compound, a C9 n-alkyl side chain containing bisphosphonate, caused an 80% reduction in parasitemia with no overt toxicity. Taken together, these results show that bisphosphonates appear to be useful lead compounds for the development of novel antiamebic and antimalarial drugs.

  DOI：

  10.1021/jm030084x